CN105418848B - A kind of method that boron trifluoride catalysis prepares C5 Petropols - Google Patents
A kind of method that boron trifluoride catalysis prepares C5 Petropols Download PDFInfo
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Abstract
The present invention relates to a kind of boron trifluorides to be catalyzed the method for preparing C5 Petropols, including：C 5 fraction rectifying is obtained into boiling point at 20~70 DEG C as polymer raw A, using styrene, α-methylstyrene, vinyltoluene enrichment material as polymer raw B, by raw material A, raw material B and saturated hydrocarbons solvent in mass ratio 1: (0~0.5): (1~1.5) is uniformly mixed to get dispensing；Then in BF3It is reacted 2~5 hours at a temperature of 50~170 DEG C under system Friedel Crafts catalyst actions, obtains polymer fluid；Again modified C5 Petropols are obtained through desolventizing, de- oligomer.Present invention process is easy, good to complicated C5 adaptability to raw material, and the C5 Petropols of high softening-point can be prepared.
Description
Technical field
The invention belongs to the preparation field of Petropols, more particularly to a kind of boron trifluoride catalysis prepares C5 Petropols
Method.
Background technology
C5 Petropols, also known as aliphatic petroleum resin are using the C 5 fraction of ethylene by-product as raw material, through cationic catalysts
It polymerize obtained middle low-molecular weight polymer, number-average molecular weight (Mn) is 300~3000.C5 Petropols have acid value it is low,
The characteristics such as good, water-fast, the resistance to ethyl alcohol of compatibility and chemical resistance corrosion, and gluing performance can be improved, it is therefore widely used in
The industries such as the tackifier and high solids coatings of rubber and adhesive, traffic paint, ink, papermaking.
In recent years, with the development in Petropols field, modification or mixing of the C 5 petroleum resin through distinct methods obtain
All kinds of nonpetroleum resins, to adapt to market to properties of product application and the requirement of economic benefit.
In US5128426, if work when Yamasaki thinks to prepare m-pentadiene petro-resin using isoprene modifying agent
Skill condition is improper to easy to produce gel, by extending anhydrous AlCl3The jitter time of initiator in organic solvent, increase feed intake
It can be obtained that dissolubility is good, and softening point is higher than 100 DEG C, and Z-average molecular weight is less than 2.7 resin the time (be more than 90 minutes).
It is described in CN86106961 using boron trifluoride and/or boron trifluoride complex as catalyst, makes petroleum distillate
It is thermally cracked to produce the fraction with personnel's boiling point within the scope of 20~280 DEG C in oil and carries out polymerization manufacture Petropols.
Petropols are prepared using the boron trifluoride of load/co-catalyst complex compound in CN1451021A, preferred co-catalyst is that have
The alcohol or carboxylic acid of machine object.Above-mentioned two patents insufficient disclosure in invention content, covering scope are wider and rough.
Invention content
Technical problem to be solved by the invention is to provide a kind of boron trifluorides to be catalyzed the method for preparing C5 Petropols, should
Method and process is easy, and the higher modified C5 Petropols of softening point are prepared.
A kind of boron trifluoride of the present invention is catalyzed the method for preparing C5 Petropols, including：
(1) boiling point for obtaining C 5 fraction rectifying in 20~70 DEG C of component as polymer raw A, with styrene, α-first
Base styrene, vinyltoluene enrichment material as polymer raw B, polymer raw A, polymer raw B and saturated hydrocarbons are molten
Agent is 1 in mass ratio: (0~0.5): (1~1.5) is uniformly mixed to get dispensing；
(2) in the reaction kettle with blender, first input account for react total quality of material 30~50% saturated hydrocarbons it is molten
Agent, then the dispensing accounted in the step of reacting total quality of material 50~70% (1) is added dropwise, while being continuously added to react total quality of material
The boron trifluoride catalyst of 0.1~2.0wt% reacts 2~5 hours at a temperature of 50~170 DEG C after feeding intake, is polymerize
Liquid；
(3) calcium hydroxide of 2~4 times of catalyst quality is put into polymer fluid into step (2), then puts into and accounts for calcium hydroxide
The methanol or ethyl alcohol of quality 1/3~2/3 obtain suspension after being sufficiently stirred 15~60min, resin liquid are obtained after filtering；
(4) by resin liquid in step (3) in rectifying column carry out solvent removal, operating pressure be -0.06MPa~-
0.09MPa, bottom temperature are 150~250 DEG C, and tower top temperature is 70~190 DEG C, and reflux ratio is 1~5, and bottom of tower is obtained containing stone
The resin liquid of oleoresin, oligomer and partial solvent；(because distillation process can not remove oligomer and recycling design completely, because
There is stripping process further to remove in this step 5, after the operation of two steps, still remaining a small amount of oligomer in resin liquid)
(5) by resin liquid in step (4) in stripper, steam distillation is carried out in the operating pressure of 0.1~0.3MPa,
Oligomer and partial solvent in step (4) are removed, C5 Petropols are obtained.
In the step (1) polymer raw A be 5.0~15.0wt% of iso-amylene, 2.0~20.0wt% of isoprene,
20.0~50.0wt% of pentadiene, 1.0~5.0wt% of cyclopentadiene, cyclopentene 5.0~15.0wt%, 1- hexene 0~
3.0wt%, remaining is C5~C6 aliphatic saturated hydrocarbons.
In the step (1) polymer raw B be 5.0~10.0wt% of styrene, 1.0~8.0wt% of α-methylstyrene,
10.0~40.0wt% of vinyltoluene, remaining is the BTX aromatics of C7~C10.
The hydrocarbon mixture that saturation hydrocarbon solvent is arbitrary C5~C10 in step (1) neutralization procedure (2).
Dispensing is 1.7~7.5wt% of iso-amylene, 0.7~10.0wt% of isoprene, pentadiene in the step (1)
6.7~25.0wt%, 0.3~2.5wt% of cyclopentadiene, cyclopentene 1.7~7.5wt%, 1- 0~1.5wt% of hexene, styrene
0~2.0wt%, 0~1.6wt% of α-methylstyrene, 0~8.0wt% of vinyltoluene, remaining is the hydrocarbon mixture of C5~C10.
The styrene derivative content of enrichment material is higher in the step (1), but non-sterling.
Boron trifluoride catalyst is gas boron trifluoride, boron trifluoride etherate or borontrifluoride in the step (2)
The BF such as boron acetonitrile complex compound3It is any one in Friedel-Crafts catalyst.
Temperature is 120~140 DEG C in the step (2), 2~3h of reaction time.
Suspension is milky to yellow suspension in the step (3)；Resin liquid is clear water white to light yellow
Resin liquid.
C5 Petropols generally use AlCl3Be Friedel-Crafts catalyst, polymerization temperature is relatively low, usually 20~
60 DEG C, 90~130 DEG C of the resin softening point of preparation.And use BF3It is Friedel-Crafts catalyst preparation C5 Petropols
The liquid resin of 70 DEG C of softening point ＜ would generally be obtained because of strong chain transfer reaction.The present invention polymerize work using high-temperature catalytic
Skill improves the molecular chain length of C5 Petropols, and the high softening point resin of 110 DEG C of softening point can be prepared.
In the present invention, suitable Styrene and its derivatives are introduced in polymer raw, using it in BF3Have in system
Preferable polymerization activity helps to improve molecular resin amount and softening point；Aromatic ring structure is introduced in the molecule simultaneously, helps to change
The compatibility of kind C5 Petropols and SIS, SBS, SBES, EVA isopolarity resin.
In the method for the present invention, step (4) and (5) are to remove not poly- raw material, solvent, oligomer in Petropols production technology
Conventional method.Wherein (5) stripper generally selects steam as stripping solvent.When using propane or ethane as stripping solvent
The oligomer residual of resin can effectively be reduced.
Advantageous effect
(1) present invention uses BF3It is the C5 Petropols that Friedel-Crafts catalyst preparations obtain high softening-point；
(2) method and process provided by the invention is easy, good to complicated C5 adaptability to raw material, can poly group divide high conversion rate；
(3) introduce appropriate aromatic ring structure in C5 Petropols in the present invention, help to improve C5 Petropols and SIS,
The compatibility of SBS, SBES, EVA isopolarity resin.
Specific implementation mode
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, people in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Table 1 is ethylene unit by-product C 5 fraction typical component：
Table 1
The typical composition that table 2 is polymer raw A：
Table 2
| Serial number | Compound name | Content, % |
| 1 | Isopentane | 6.52 |
| 2 | 1- amylenes | 0.53 |
| 3 | Iso-amylene | 7.82 |
| 4 | Pentane | 18.06 |
| 5 | Isoprene | 9.15 |
| 6 | 1,3- pentadienes | 33.10 |
| 7 | Cyclopentadiene | 2.29 |
| 8 | Cyclopentene | 12.72 |
| 9 | 1- hexenes | 1.51 |
| 10 | Remaining C5~C6 hydrocarbon | 8.30 |
Raw material extraction process：
Cracking of ethylene by-product light dydrocarbon raw material cuts to obtain the component that boiling point is 20~70 DEG C to be the present invention through air-distillation
Use polymer raw A.
The typical composition for the polymer raw B that table 3 is styrene, methyl styrene is enriched with：
Table 3
Embodiment 1
C 5 fraction rectifying is obtained into boiling point and is used as polymer raw A at 20~70 DEG C, with styrene, α-methylstyrene, second
The enrichment material of alkenyl toluene is equal by raw material A, raw material B and saturated hydrocarbons solvent C in mass ratio 1: 0.5: 1 as polymer raw B
Even to be mixed to get dispensing D, ingredient is：Iso-amylene 6.0wt%, isoprene 8.0wt%, pentadiene 20.0wt%, ring penta
Diene 2.0wt%, cyclopentene 6.0wt%, 1- hexene 1.2wt%, styrene 2.0wt%, α-methylstyrene 1.6wt%, second
Alkenyl toluene 8.0wt%, remaining is the hydrocarbon mixture of C5~C10；
In the reaction kettle with blender, input accounts for the saturated hydrocarbons solvent for reacting total quality of material 50% in advance, then
The dispensing D for reacting total quality of material 49.5% is accounted for by being slowly added dropwise, while being continuously added to the borontrifluoride of total quality of material 0.5wt%
B catalyst enables reaction mass be reacted 4 hours at a temperature of 130 DEG C, obtains polymer fluid after feeding intake；Into above-mentioned polymer fluid
The calcium hydroxide of 4 times of catalyst quality is put into, then puts into the methanol for accounting for calcium hydroxide quality 1/3, is obtained after being sufficiently stirred 30min
Milky is to yellow suspension；The suspension is by obtaining clear water white to light yellow resin liquid after filtering；By resin liquid
Solvent removal is carried out in rectifying column, operating pressure is -0.09Mpa, and bottom temperature is 200 DEG C, and tower top temperature is 70 DEG C, reflux ratio
It is 2, bottom of tower obtains the resin liquid containing Petropols, oligomer and a small amount of solvent；By resin liquid in stripper, in 0.1Mpa
Operating pressure carry out steam distillation, it is 113 DEG C to remove after above-mentioned oligomer and solvent up to softening point, gardner color number
The modification C5 Petropols of 6.4#.
Embodiment 2
C 5 fraction rectifying is obtained into boiling point and is used as polymer raw A at 20~70 DEG C, with styrene, α-methylstyrene, second
The enrichment material of alkenyl toluene is equal by raw material A, raw material B and saturated hydrocarbons solvent C in mass ratio 1: 0: 1.5 as polymer raw B
Even to be mixed to get dispensing D, ingredient is：Iso-amylene 6.0wt%, isoprene 8.0wt%, pentadiene 20.0wt%, ring penta
Diene 2.0wt%, cyclopentene 6.0wt%, 1- hexene 1.2wt%, remaining is the hydrocarbon mixture of C5~C10；
In the reaction kettle with blender, input accounts for the saturated hydrocarbons solvent for reacting total quality of material 50% in advance, then
The dispensing D for reacting total quality of material 49.5% is accounted for by being slowly added dropwise, while being continuously added to the borontrifluoride of total quality of material 0.5wt%
B catalyst enables reaction mass be reacted 4 hours at a temperature of 130 DEG C, obtains polymer fluid after feeding intake；Into above-mentioned polymer fluid
The calcium hydroxide of 4 times of catalyst quality is put into, then puts into the methanol for accounting for calcium hydroxide quality 1/3, is obtained after being sufficiently stirred 30min
Milky is to yellow suspension；The suspension is by obtaining clear water white to light yellow resin liquid after filtering；By resin liquid
Solvent removal is carried out in rectifying column, operating pressure is -0.09Mpa, and bottom temperature is 170 DEG C, and tower top temperature is 70 DEG C, reflux ratio
It is 2, bottom of tower obtains the resin liquid containing Petropols, oligomer and a small amount of solvent；By resin liquid in stripper, in 0.1Mpa
Operating pressure carry out steam distillation, it is 96.5 DEG C to remove after above-mentioned oligomer and solvent up to softening point, gardner color number
The C5 Petropols of 7.3#.
Embodiment 3
C 5 fraction rectifying is obtained into boiling point and is used as polymer raw A at 20~70 DEG C, with styrene, α-methylstyrene, second
The enrichment material of alkenyl toluene is equal by raw material A, raw material B and saturated hydrocarbons solvent C in mass ratio 1: 0: 1.5 as polymer raw B
Even to be mixed to get dispensing D, ingredient is：Iso-amylene 5.2wt%, isoprene 4.8wt%, pentadiene 15.2wt%, ring penta
Diene 1.6wt%, cyclopentene 6.0wt%, 1- hexene 0.5wt%, remaining is the hydrocarbon mixture of C5~C10；
In the reaction kettle with blender, input accounts for the saturated hydrocarbons solvent for reacting total quality of material 50% in advance, then
The dispensing D for reacting total quality of material 48.5% is accounted for by being slowly added dropwise, while being continuously added to the borontrifluoride of total quality of material 1.5wt%
Borate ether catalyst enables reaction mass be reacted 5 hours at a temperature of 50 DEG C, obtains polymer fluid after feeding intake；To above-mentioned polymerization
The calcium hydroxide of 3 times of catalyst quality of input in liquid, then the methanol for accounting for calcium hydroxide quality 1/2 is put into, after being sufficiently stirred 30min
Milky is obtained to yellow suspension；The suspension is by obtaining clear water white to light yellow resin liquid after filtering；It will tree
Fat liquid carries out solvent removal in rectifying column, and operating pressure is -0.09Mpa, and bottom temperature is 170 DEG C, and tower top temperature is 70 DEG C, is returned
For stream than being 2, bottom of tower obtains the resin liquid containing Petropols, oligomer and a small amount of solvent；By resin liquid in stripper, in
The operating pressure of 0.1Mpa carries out steam distillation, and it is 50 DEG C of ＜ to remove after above-mentioned oligomer and solvent up to softening point, adds moral
Receive the liquid C5 Petropols of color 3.8#.
Embodiment 4
C 5 fraction rectifying is obtained into boiling point and is used as polymer raw A at 20~70 DEG C, with styrene, α-methylstyrene, second
The enrichment material of alkenyl toluene is as polymer raw B, by raw material A, raw material B and saturated hydrocarbons solvent C in mass ratio 1: 0.3: 1.5
It uniformly is mixed to get dispensing D, ingredient is：Iso-amylene 4.6wt%, isoprene 4.3wt%, pentadiene 16.0wt%, ring
Pentadiene 1.4wt%, cyclopentene 5.2wt%, 1- hexene 0.7wt%, styrene 1.2wt%, α-methylstyrene 1.0wt%,
Vinyltoluene 4.5wt%, remaining is the hydrocarbon mixture of C5~C10；
In the reaction kettle with blender, input accounts for the saturated hydrocarbons solvent for reacting total quality of material 50% in advance, then
The dispensing D for reacting total quality of material 48.5% is accounted for by being slowly added dropwise, while being continuously added to the borontrifluoride of total quality of material 1.5wt%
Borate ether catalyst enables reaction mass be reacted 5 hours at a temperature of 50 DEG C, obtains polymer fluid after feeding intake；To above-mentioned polymerization
The calcium hydroxide of 3 times of catalyst quality of input in liquid, then the methanol for accounting for calcium hydroxide quality 1/2 is put into, after being sufficiently stirred 30min
Milky is obtained to yellow suspension；The suspension is by obtaining clear water white to light yellow resin liquid after filtering；It will tree
Fat liquid carries out solvent removal in rectifying column, and operating pressure is -0.09Mpa, and bottom temperature is 200 DEG C, and tower top temperature is 70 DEG C, is returned
For stream than being 2, bottom of tower obtains the resin liquid containing Petropols, oligomer and a small amount of solvent；By resin liquid in stripper, in
The operating pressure of 0.1Mpa carries out steam distillation, removes after above-mentioned oligomer and solvent up to 86 DEG C of softening point, gardner color
The C5 Petropols of number 4.5#.
Embodiment 5
C 5 fraction rectifying is obtained into boiling point and is used as polymer raw A at 20~70 DEG C, with styrene, α-methylstyrene, second
The enrichment material of alkenyl toluene is equal by raw material A, raw material B and saturated hydrocarbons solvent C in mass ratio 1: 0.5: 1 as polymer raw B
Even to be mixed to get dispensing D, ingredient is：Iso-amylene 6.0wt%, isoprene 8.0wt%, pentadiene 20.0wt%, ring penta
Diene 2.0wt%, cyclopentene 6.0wt%, 1- hexene 1.2wt%, styrene 2.0wt%, α-methylstyrene 1.6wt%, second
Alkenyl toluene 8.0wt%, remaining is the hydrocarbon mixture of C5~C10；
In the reaction kettle with blender, input accounts for the saturated hydrocarbons solvent for reacting total quality of material 45% in advance, then
The dispensing D for reacting total quality of material 54.5% is accounted for by being slowly added dropwise, while being continuously added to the borontrifluoride of total quality of material 0.5wt%
B catalyst enables reaction mass be reacted 2 hours at a temperature of 75 DEG C, obtains polymer fluid after feeding intake；Into above-mentioned polymer fluid
The calcium hydroxide of 4 times of catalyst quality is put into, then puts into the methanol for accounting for calcium hydroxide quality 1/3, is obtained after being sufficiently stirred 30min
Milky is to yellow suspension；The suspension is by obtaining clear water white to light yellow resin liquid after filtering；By resin liquid
Solvent removal is carried out in rectifying column, operating pressure is -0.09Mpa, and bottom temperature is 220 DEG C, and tower top temperature is 110 DEG C, reflux
Than being 2, bottom of tower obtains the resin liquid containing Petropols, oligomer and a small amount of solvent；By resin liquid in stripper, in
The operating pressure of 0.3Mpa carries out steam distillation, and it is 89 DEG C to remove after above-mentioned oligomer and solvent up to softening point, Gardner
Color 5.2#, number-average molecular weight Mn are 820, the modification C5 Petropols of molecular weight distribution mw/mn=1.79.
Claims (5)
1. a kind of boron trifluoride is catalyzed the method for preparing C5 Petropols, including：
(1) boiling point for obtaining C 5 fraction rectifying in 20~70 DEG C of component as polymer raw A, with styrene, Alpha-Methyl benzene
Ethylene, vinyltoluene enrichment material as polymer raw B, polymer raw A, polymer raw B and saturated hydrocarbons solvent are pressed
Mass ratio is 1: 0: (1~1.5) is uniformly mixed to get dispensing；Wherein, polymer raw A is 5.0~15.0wt% of iso-amylene, isoamyl
2.0~20.0wt% of diene, 20.0~50.0wt% of pentadiene, 1.0~5.0wt% of cyclopentadiene, cyclopentene 5.0~
15.0wt%, 1- 0~3.0wt% of hexene, remaining is C5~C6 aliphatic saturated hydrocarbons；
(2) in the reaction kettle with blender, first input accounts for the saturated hydrocarbons solvent for reacting total quality of material 30~50%, then
Dropwise addition accounts for the dispensing in the step of reacting total quality of material 50~70% (1), at the same be continuously added to react total quality of material 0.1~
The boron trifluoride catalyst of 2.0wt% reacts 2~3h at a temperature of 120~140 DEG C, obtains polymer fluid after feeding intake；
(3) calcium hydroxide of 2~4 times of catalyst quality is put into polymer fluid into step (2), then puts into and accounts for calcium hydroxide quality
1/3~2/3 methanol or ethyl alcohol obtains suspension after being sufficiently stirred 15~60min, resin liquid is obtained after filtering；
(4) resin liquid in step (3) is subjected to solvent removal in rectifying column, operating pressure is -0.06MPa~-0.09MPa, tower
Kettle temperature degree is 150~250 DEG C, and tower top temperature is 70~190 DEG C, and reflux ratio is 1~5, and bottom of tower obtains containing Petropols, oligomeric
The resin liquid of object and partial solvent；
(5) by resin liquid in step (4) in stripper, steam distillation is carried out in the operating pressure of 0.1~0.3MPa, is removed
Oligomer and partial solvent in step (4), obtain C5 Petropols.
2. a kind of boron trifluoride according to claim 1 is catalyzed the method for preparing C5 Petropols, which is characterized in that described
In step (1) dispensing be 1.7~7.5wt% of iso-amylene, 0.7~10.0wt% of isoprene, pentadiene 6.7~
25.0wt%, 0.3~2.5wt% of cyclopentadiene, cyclopentene 1.7~7.5wt%, 1- 0~1.5wt% of hexene, styrene
0wt%, α-methylstyrene 0wt%, vinyltoluene 0wt%, remaining is the hydrocarbon mixture of C5~C10.
3. a kind of boron trifluoride according to claim 1 is catalyzed the method for preparing C5 Petropols, which is characterized in that described
The hydrocarbon mixture that saturation hydrocarbon solvent is arbitrary C5~C10 in step (1) and step (2).
4. a kind of boron trifluoride according to claim 1 is catalyzed the method for preparing C5 Petropols, which is characterized in that described
Boron trifluoride catalyst is BF in step (2)3It is any one in Friedel-Crafts catalyst.
5. a kind of boron trifluoride according to claim 4 is catalyzed the method for preparing C5 Petropols, which is characterized in that described
BF3 systems Friedel-Crafts catalyst is gas boron trifluoride, boron trifluoride etherate or boron trifluoride acetonitrile complexing
Object.
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| CN110563875A (en) * | 2019-09-20 | 2019-12-13 | 宁波甬华树脂有限公司 | Preparation method of modified aromatic hydrocarbon petroleum resin |
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| CN106699973B (en) * | 2016-11-17 | 2019-01-29 | 恒河材料科技股份有限公司 | A kind of preparation method of low molecular weight C5/C10 copolymer resins |
| CN106699972B (en) * | 2016-11-17 | 2019-04-12 | 恒河材料科技股份有限公司 | A kind of preparation method and its device of C5/C10 copolymer resins |
| CN112851858B (en) * | 2021-01-13 | 2022-09-16 | 淄博鲁华泓锦新材料集团股份有限公司 | C5 petroleum resin takes off system of urging |
| CN114230705A (en) * | 2021-12-15 | 2022-03-25 | 恒河材料科技股份有限公司 | Preparation method of flexible poly alpha-methylstyrene resin |
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| US4419503A (en) * | 1982-05-24 | 1983-12-06 | Exxon Research & Engineering Co. | Catalytic process for the production of petroleum resins |
| JPH05140238A (en) * | 1991-11-19 | 1993-06-08 | Tosoh Corp | Production of aliphatic petroleum resin |
| CN101891863A (en) * | 2010-06-13 | 2010-11-24 | 宁波职业技术学院 | Method for preparing styrene modified C5 petroleum resin |
| CN102718924B (en) * | 2012-06-27 | 2014-01-29 | 浙江恒河石油化工股份有限公司 | Method for preparing C5/C9 copolymerized petroleum resin |
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| CN110563875A (en) * | 2019-09-20 | 2019-12-13 | 宁波甬华树脂有限公司 | Preparation method of modified aromatic hydrocarbon petroleum resin |
| CN110563875B (en) * | 2019-09-20 | 2021-12-21 | 宁波甬华树脂有限公司 | Preparation method of modified aromatic hydrocarbon petroleum resin |
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